Methanesulfonic Acid → Diisopropyl Ether

HRID 2413422Notes

Reaction equation

HRID 2413422 reaction equation
[NH:1]([C:8]1[S:9][C:10]([C:13]2[CH2:20][S:19][CH:18]3[N:15]([C:16](=[O:29])[CH:17]3[NH:21][C:22](OC(C)(C)C)=[O:23])[C:14]=2[C:30]([O:32][CH:33]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[CH:11][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:46]S(O)(=O)=O.[S:51]1[CH:55]=[CH:54][CH:53]=[C:52]1[CH2:56]C(Cl)=O.C(N(CC)CC)C>C(#N)C.O1CCCC1>[CH:33]([O:32][CH:30]([CH3:14])[CH3:46])([CH3:34])[CH3:40].[NH:1]([C:8]1[S:9][C:10]([C:13]2[CH2:20][S:19][CH:18]3[N:15]([C:16](=[O:29])[CH:17]3[NH:21][C:22](=[O:23])[CH2:56][C:52]3[S:51][CH:55]=[CH:54][CH:53]=3)[C:14]=2[C:30]([O:32][CH:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[O:31])=[CH:11][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 1623622-Thiopheneacetyl chlorideHCID 13175942HCID 13175942, compound

Product 2

HCID 7914Diisopropyl EtherHCID 13175960HCID 13175960, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Anilino-thiazol-5-yl)-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene (2.3 g) is treated with methanesulphonic acid (2.3 cc) in acetonitrile (23 cc) in accordance with the working method described in Example 2. Crude 7-amino-3-(2-anilino-thiazol-5-yl)-2-benzhydryloxycarbonyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (1.85 g) is obtained and is acylated with (thien-2-yl)-acetyl chloride (0.445 cc) in tetrahydrofuran (25 cc) in the presence of triethylamine (0.505 cc), using the working method described in Example 1. The crude product obtained is chromatographed on a column (height: 30 cm; diameter: 2.5 cm) of silica gel (0.04-0.06 mm), elution being carried out under a pressure of 1.2 bar (120 kPa) with a 70:30 (by volume) mixture (3 liters) of cyclohexane and ethyl acetate, and 50 cc fractions being collected. Fractions 20 to 50 are combined and concentrated to dryness. After trituration with isopropyl ether, 3-(2-anilino-thiazol-5-yl)-2-benzhydryloxycarbonyl-8-oxo-7-(thien-2 -yl-acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene (0.9 g) is obtained in the form of a yellow solid.

Workup

  1. customCrude 7-amino-3-(2-anilino-thiazol-5-yl)-2-benzhydryloxycarbonyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (1.85 g) is obtained
  2. customThe crude product obtained
  3. customis chromatographed on a column (height: 30 cm; diameter: 2.5 cm) of silica gel (0.04-0.06 mm), elution
  4. custombeing collected
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-944487272ec448ed811288a8408b4c38
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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